Cyclopropanemethanamine → HCID 24738345, compound

HRID 731619Notes

Reaction equation

HRID 731619 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[C:19]([C:21]([OH:23])=O)[CH:18]=[CH:17][N:16]2[CH:24]=1.C(N(CC)C(C)C)(C)C.[NH2:34][CH2:35][CH:36]1[CH2:38][CH2:37]1.[Cl-].[Na+].O.O>CN(C=O)C>[CH:36]1([CH2:35][NH:34][C:21]([C:19]2[CH:18]=[CH:17][N:16]3[CH:24]=[C:13]([C:3]4[C:4]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=5)=[N:5][O:6][C:2]=4[CH3:1])[N:14]=[C:15]3[CH:20]=2)=[O:23])[CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 23713072Sodium chloride dihydrateHCID 69067892HCID 69067892, compound

Product 1

HCID 24738345HCID 24738345, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine-7-carboxylic acid (64 mg, 0.2 mmol) in DMF (0.3 mL) was added N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uranium tetrafluoroborate (71 mg, 0.22 mmol), N,N-diisopropyl ethyl amine (129 mg, 1.0 mmol) and aminomethylcyclopropane (19 μL, 0.22 mmol) and the resulting mixture stirred at room temperature for 1 h. The resulting mixture was then poured into a mixture of brine:water (1:1) and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulphate and evaporated to leave a yellow oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75) afforded the title compound (55 mg, 74%) which was obtained as a yellow solid. MS: m/e=373.1 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were then washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto leave a yellow oil
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75)

Sources & evidence

ORD record
ord-511f2c83d1eb4e12afa7d6eb6b6e256c
Source dataset
uspto-grants-2009_09
Patent number
US07585874B2

Reaction notes

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